NPASS Compound

Structure

NPC472668 OpenBabel07101719512D 39 44 0 0 1 0 0 0 0 0999 V2000 -4.4372 1.4453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7436 3.4009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8430 -1.8367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7963 -2.0542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2944 -0.3404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6010 2.8274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2033 -0.0214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4614 0.8596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9587 3.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5081 1.0772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9587 4.4462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3014 1.4453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8969 -0.9991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4541 3.9573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4372 2.4231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8969 3.8897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0288 3.1663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7266 2.2363 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7436 -0.5103 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0501 -0.5103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7266 0.6543 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8856 -0.0214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8969 1.9342 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8969 0.9564 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0501 2.4231 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5081 -1.1199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7436 0.4675 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2033 1.9342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0501 0.4675 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2033 0.9564 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2840 2.9120 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8969 4.8675 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2033 -0.9991 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8634 -0.0214 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0288 4.7483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5904 2.9120 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0501 3.4009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4614 -0.9023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 7 29 1 0 0 0 0 8 10 2 0 0 0 0 8 22 1 0 0 0 0 9 11 2 0 0 0 0 9 17 1 0 0 0 0 10 27 1 0 0 0 0 11 35 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 14 17 2 0 0 0 0 14 35 1 0 0 0 0 15 31 2 0 0 0 0 15 36 1 0 0 0 0 16 32 2 0 0 0 0 16 37 1 0 0 0 0 17 18 1 0 0 0 0 18 28 1 6 0 0 0 19 26 1 0 0 0 0 19 27 1 1 0 0 0 20 29 1 0 0 0 0 20 33 2 0 0 0 0 21 30 1 6 0 0 0 21 38 1 0 0 0 0 22 34 2 0 0 0 0 22 39 1 0 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 23 36 1 1 0 0 0 24 27 1 1 0 0 0 24 29 1 0 0 0 0 25 28 1 6 0 0 0 25 37 1 0 0 0 0 26 39 1 0 0 0 0 27 5 1 1 0 0 0 28 30 1 6 0 0 0 29 30 1 6 0 0 0 30 38 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	540.24
Volume:	536.754
LogP:	3.169
LogD:	1.67
LogS:	-4.227
# Rotatable Bonds:	5
TPSA:	121.64
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.319
Synthetic Accessibility Score:	5.884
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.281
MDCK Permeability:	7.640738476766273e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	0.503

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	78.4278335571289%
Volume Distribution (VD):	1.795
Pgp-substrate:	15.58950424194336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.065
CYP2C19-inhibitor:	0.432
CYP2C19-substrate:	0.417
CYP2C9-inhibitor:	0.905
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.295
CYP2D6-substrate:	0.066
CYP3A4-inhibitor:	0.881
CYP3A4-substrate:	0.681

ADMET: Excretion

Clearance (CL):	5.234
Half-life (T1/2):	0.879

ADMET: Toxicity

hERG Blockers:	0.468
Human Hepatotoxicity (H-HT):	0.966
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.34
Carcinogencity:	0.033
Eye Corrosion:	0.012
Eye Irritation:	0.074
Respiratory Toxicity:	0.973

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC472668

Natural Product ID:	NPC472668
*Common Name:**	HVRLWIKUVGRWEG-BSHVTPGASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HVRLWIKUVGRWEG-BSHVTPGASA-N
Standard InCHI:	InChI=1S/C30H36O9/c1-15(31)36-23-24-27(5)10-8-22(34)39-26(3,4)19(27)13-20(33)29(24,7)30-21(38-30)12-18(17-9-11-35-14-17)28(30,6)25(23)37-16(2)32/h8-11,14,18-19,21,23-25H,12-13H2,1-7H3/t18-,19-,21+,23+,24+,25-,27-,28+,29+,30+/m0/s1
SMILES:	CC(=O)O[C@@H]1[C@@H]2[C@@]3(C)C=CC(=O)OC([C@@H]3CC(=O)[C@@]2(C)[C@@]23[C@]([C@H]1OC(=O)C)(C)[C@@H](C[C@H]3O2)c1ccoc1)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581411
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9173	Munronia henryi	Species	Meliaceae	Eukaryota	whole plants	Wenshan, Yunnan Province, China	2012-Nov	PMID[25798528]
NPO9173	Munronia henryi	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	6
Others	11

Activity Type	# Activity
Cell Line	5
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[515596]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[515596]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[515596]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[515596]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	10000.0	nM	PMID[515596]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	98.9	%	PMID[515596]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	98.2	%	PMID[515596]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	56.7	%	PMID[515596]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	52.8	%	PMID[515596]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	95.6	%	PMID[515596]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	92.3	%	PMID[515596]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	86.1	%	PMID[515596]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	62.3	%	PMID[515596]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	30.9	%	PMID[515596]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	11.8	%	PMID[515596]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	IC50	=	19.6	ug.mL-1	PMID[515596]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Ratio IC50	=	2.0	n.a.	PMID[515596]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC472668 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	429
0.1-0.2	1559
0.2-0.3	3412
0.3-0.4	6323
0.4-0.5	11211
0.5-0.6	9777
0.6-0.7	8670
0.7-0.8	943
0.8-0.85	266
0.85-0.9	88
0.9-0.95	14
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9804	High Similarity	NPC472669
0.961	High Similarity	NPC471166
0.961	High Similarity	NPC471167
0.9548	High Similarity	NPC471168
0.9408	High Similarity	NPC84063
0.9231	High Similarity	NPC474932
0.9216	High Similarity	NPC18135
0.9161	High Similarity	NPC471175
0.915	High Similarity	NPC156189
0.9136	High Similarity	NPC469848
0.9103	High Similarity	NPC175964
0.9103	High Similarity	NPC204663
0.9103	High Similarity	NPC471169
0.9045	High Similarity	NPC195131
0.9006	High Similarity	NPC472764
0.9006	High Similarity	NPC476224
0.8994	High Similarity	NPC197596
0.8981	High Similarity	NPC126723
0.8961	High Similarity	NPC470791
0.8961	High Similarity	NPC470790
0.8954	High Similarity	NPC221809
0.8951	High Similarity	NPC472765
0.8951	High Similarity	NPC472766
0.8924	High Similarity	NPC167142
0.8917	High Similarity	NPC476262
0.891	High Similarity	NPC29695
0.891	High Similarity	NPC182427
0.891	High Similarity	NPC476201
0.891	High Similarity	NPC268905
0.8896	High Similarity	NPC472659
0.8882	High Similarity	NPC259943
0.8875	High Similarity	NPC6326
0.8875	High Similarity	NPC5741
0.8875	High Similarity	NPC472767
0.8868	High Similarity	NPC475226
0.8868	High Similarity	NPC473473
0.8868	High Similarity	NPC475295
0.8848	High Similarity	NPC471632
0.8841	High Similarity	NPC285227
0.8834	High Similarity	NPC327922
0.8831	High Similarity	NPC255414
0.882	High Similarity	NPC469846
0.882	High Similarity	NPC476197
0.882	High Similarity	NPC165218
0.8817	High Similarity	NPC242068
0.8817	High Similarity	NPC105395
0.8817	High Similarity	NPC247563
0.8805	High Similarity	NPC286722
0.8805	High Similarity	NPC299038
0.879	High Similarity	NPC322546
0.879	High Similarity	NPC308205
0.8782	High Similarity	NPC476122
0.878	High Similarity	NPC470995
0.8765	High Similarity	NPC476860
0.8758	High Similarity	NPC470939
0.8758	High Similarity	NPC472771
0.875	High Similarity	NPC237155
0.875	High Similarity	NPC472671
0.8742	High Similarity	NPC107646
0.8742	High Similarity	NPC209364
0.8742	High Similarity	NPC263265
0.8735	High Similarity	NPC236004
0.8735	High Similarity	NPC94763
0.8727	High Similarity	NPC159232
0.8726	High Similarity	NPC116717
0.8718	High Similarity	NPC471001
0.8718	High Similarity	NPC472654
0.8718	High Similarity	NPC125182
0.8718	High Similarity	NPC69647
0.8712	High Similarity	NPC478178
0.8712	High Similarity	NPC149945
0.8712	High Similarity	NPC23387
0.8704	High Similarity	NPC472773
0.8696	High Similarity	NPC470789
0.8696	High Similarity	NPC475381
0.8696	High Similarity	NPC472653
0.8688	High Similarity	NPC475066
0.8688	High Similarity	NPC469847
0.8688	High Similarity	NPC470118
0.8679	High Similarity	NPC469850
0.8667	High Similarity	NPC472650
0.8659	High Similarity	NPC476850
0.8659	High Similarity	NPC476853
0.8659	High Similarity	NPC478179
0.8659	High Similarity	NPC173516
0.8659	High Similarity	NPC472651
0.8659	High Similarity	NPC476861
0.8659	High Similarity	NPC472774
0.8659	High Similarity	NPC472775
0.865	High Similarity	NPC476856
0.865	High Similarity	NPC476858
0.865	High Similarity	NPC476857
0.8642	High Similarity	NPC200782
0.8642	High Similarity	NPC82851
0.8639	High Similarity	NPC470938
0.8631	High Similarity	NPC478177
0.8623	High Similarity	NPC469576
0.8623	High Similarity	NPC477824
0.8623	High Similarity	NPC471437
0.8606	High Similarity	NPC271235
0.8606	High Similarity	NPC472652
0.8606	High Similarity	NPC160651
0.8606	High Similarity	NPC472673
0.8606	High Similarity	NPC471397
0.8598	High Similarity	NPC472141
0.859	High Similarity	NPC470941
0.8589	High Similarity	NPC51568
0.8589	High Similarity	NPC134254
0.8589	High Similarity	NPC39986
0.8589	High Similarity	NPC234660
0.8589	High Similarity	NPC302369
0.858	High Similarity	NPC305016
0.858	High Similarity	NPC191828
0.858	High Similarity	NPC25255
0.8571	High Similarity	NPC214495
0.8571	High Similarity	NPC195954
0.8571	High Similarity	NPC469633
0.8571	High Similarity	NPC470119
0.8571	High Similarity	NPC80635
0.8571	High Similarity	NPC472772
0.8553	High Similarity	NPC75906
0.8553	High Similarity	NPC472672
0.8544	High Similarity	NPC159927
0.8544	High Similarity	NPC477404
0.8544	High Similarity	NPC196864
0.8544	High Similarity	NPC469335
0.8537	High Similarity	NPC123088
0.8537	High Similarity	NPC271657
0.8535	High Similarity	NPC19747
0.8528	High Similarity	NPC470792
0.8528	High Similarity	NPC188649
0.8528	High Similarity	NPC193798
0.8528	High Similarity	NPC18347
0.8528	High Similarity	NPC149896
0.8528	High Similarity	NPC5079
0.8526	High Similarity	NPC470999
0.8521	High Similarity	NPC470181
0.8519	High Similarity	NPC475967
0.8516	High Similarity	NPC251865
0.8509	High Similarity	NPC60973
0.8506	High Similarity	NPC121158
0.85	High Similarity	NPC282445
0.85	High Similarity	NPC302054
0.85	High Similarity	NPC57998
0.85	High Similarity	NPC253201
0.8491	Intermediate Similarity	NPC291150
0.8485	Intermediate Similarity	NPC214600
0.8476	Intermediate Similarity	NPC288602
0.8476	Intermediate Similarity	NPC472139
0.8476	Intermediate Similarity	NPC469338
0.8476	Intermediate Similarity	NPC224394
0.8476	Intermediate Similarity	NPC663
0.8476	Intermediate Similarity	NPC292389
0.8476	Intermediate Similarity	NPC88841
0.8466	Intermediate Similarity	NPC335761
0.8462	Intermediate Similarity	NPC167340
0.8462	Intermediate Similarity	NPC5676
0.8462	Intermediate Similarity	NPC34056
0.8457	Intermediate Similarity	NPC249021
0.8457	Intermediate Similarity	NPC472776
0.8457	Intermediate Similarity	NPC187149
0.8457	Intermediate Similarity	NPC472778
0.8457	Intermediate Similarity	NPC472777
0.8457	Intermediate Similarity	NPC472283
0.8457	Intermediate Similarity	NPC197137
0.8457	Intermediate Similarity	NPC88007
0.8447	Intermediate Similarity	NPC296807
0.8447	Intermediate Similarity	NPC264943
0.8447	Intermediate Similarity	NPC92979
0.8447	Intermediate Similarity	NPC155939
0.8447	Intermediate Similarity	NPC141538
0.8438	Intermediate Similarity	NPC33938
0.8438	Intermediate Similarity	NPC471002
0.8438	Intermediate Similarity	NPC469503
0.8434	Intermediate Similarity	NPC270312
0.8434	Intermediate Similarity	NPC472282
0.8434	Intermediate Similarity	NPC473753
0.8434	Intermediate Similarity	NPC473766
0.8428	Intermediate Similarity	NPC5180
0.8428	Intermediate Similarity	NPC470997
0.8424	Intermediate Similarity	NPC276735
0.8424	Intermediate Similarity	NPC276551
0.8424	Intermediate Similarity	NPC469849
0.8424	Intermediate Similarity	NPC470940
0.8424	Intermediate Similarity	NPC470182
0.8424	Intermediate Similarity	NPC126984
0.8424	Intermediate Similarity	NPC27541
0.8424	Intermediate Similarity	NPC62692
0.8415	Intermediate Similarity	NPC329938
0.8415	Intermediate Similarity	NPC117986
0.8415	Intermediate Similarity	NPC96443
0.8415	Intermediate Similarity	NPC68848
0.8415	Intermediate Similarity	NPC290400
0.8405	Intermediate Similarity	NPC307383
0.8393	Intermediate Similarity	NPC475237
0.8393	Intermediate Similarity	NPC475641
0.8385	Intermediate Similarity	NPC237259
0.8385	Intermediate Similarity	NPC34421
0.8385	Intermediate Similarity	NPC98206
0.8383	Intermediate Similarity	NPC242334

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC472668 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	1029
0.2-0.3	2352
0.3-0.4	2727
0.4-0.5	1742
0.5-0.6	725
0.6-0.7	207
0.7-0.8	8
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8562	High Similarity	NPD5760	Phase 2
0.8562	High Similarity	NPD5761	Phase 2
0.8011	Intermediate Similarity	NPD8434	Phase 2
0.7811	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6764	Approved
0.7727	Intermediate Similarity	NPD6765	Approved
0.7556	Intermediate Similarity	NPD6784	Approved
0.7556	Intermediate Similarity	NPD6785	Approved
0.7268	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5494	Approved
0.7219	Intermediate Similarity	NPD920	Approved
0.7102	Intermediate Similarity	NPD919	Approved
0.7101	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6599	Discontinued
0.7069	Intermediate Similarity	NPD7819	Suspended
0.7066	Intermediate Similarity	NPD4628	Phase 3
0.7022	Intermediate Similarity	NPD1247	Approved
0.7022	Intermediate Similarity	NPD8127	Discontinued
0.7017	Intermediate Similarity	NPD7799	Discontinued
0.6982	Remote Similarity	NPD643	Clinical (unspecified phase)
0.698	Remote Similarity	NPD8404	Phase 2
0.6971	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6273	Approved
0.6957	Remote Similarity	NPD6559	Discontinued
0.6957	Remote Similarity	NPD7685	Pre-registration
0.6949	Remote Similarity	NPD7075	Discontinued
0.6888	Remote Similarity	NPD7497	Discontinued
0.6886	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1471	Phase 3
0.6882	Remote Similarity	NPD7236	Approved
0.6868	Remote Similarity	NPD7473	Discontinued
0.686	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD3926	Phase 2
0.6842	Remote Similarity	NPD6799	Approved
0.6836	Remote Similarity	NPD3817	Phase 2
0.6831	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2796	Approved
0.6818	Remote Similarity	NPD6801	Discontinued
0.6805	Remote Similarity	NPD1243	Approved
0.6793	Remote Similarity	NPD5844	Phase 1
0.6782	Remote Similarity	NPD7239	Suspended
0.6766	Remote Similarity	NPD2799	Discontinued
0.676	Remote Similarity	NPD3749	Approved
0.6743	Remote Similarity	NPD3226	Approved
0.6742	Remote Similarity	NPD5402	Approved
0.674	Remote Similarity	NPD7199	Phase 2
0.6739	Remote Similarity	NPD3818	Discontinued
0.6724	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2534	Approved
0.6705	Remote Similarity	NPD2532	Approved
0.6705	Remote Similarity	NPD2533	Approved
0.6704	Remote Similarity	NPD3882	Suspended
0.6704	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6232	Discontinued
0.6687	Remote Similarity	NPD6832	Phase 2
0.6686	Remote Similarity	NPD6002	Phase 3
0.6686	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5763	Approved
0.6686	Remote Similarity	NPD6005	Phase 3
0.6686	Remote Similarity	NPD6004	Phase 3
0.6686	Remote Similarity	NPD5762	Approved
0.6685	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8032	Phase 2
0.6667	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD1934	Approved
0.6614	Remote Similarity	NPD8312	Approved
0.6614	Remote Similarity	NPD8313	Approved
0.6611	Remote Similarity	NPD4966	Approved
0.6611	Remote Similarity	NPD4965	Approved
0.6611	Remote Similarity	NPD4967	Phase 2
0.661	Remote Similarity	NPD4380	Phase 2
0.661	Remote Similarity	NPD7028	Phase 2
0.6609	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD2801	Approved
0.6588	Remote Similarity	NPD2346	Discontinued
0.6579	Remote Similarity	NPD8407	Phase 2
0.6575	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.657	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD3748	Approved
0.6559	Remote Similarity	NPD3751	Discontinued
0.6554	Remote Similarity	NPD7458	Discontinued
0.6538	Remote Similarity	NPD6234	Discontinued
0.6536	Remote Similarity	NPD37	Approved
0.6534	Remote Similarity	NPD5403	Approved
0.6529	Remote Similarity	NPD1551	Phase 2
0.6528	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6808	Phase 2
0.6522	Remote Similarity	NPD3787	Discontinued
0.6515	Remote Similarity	NPD8285	Discontinued
0.6514	Remote Similarity	NPD5401	Approved
0.6514	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD2800	Approved
0.651	Remote Similarity	NPD8150	Discontinued
0.6508	Remote Similarity	NPD8368	Discontinued
0.6491	Remote Similarity	NPD2344	Approved
0.6489	Remote Similarity	NPD7074	Phase 3
0.6488	Remote Similarity	NPD6355	Discontinued
0.6474	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4110	Phase 3
0.6471	Remote Similarity	NPD7033	Discontinued
0.6467	Remote Similarity	NPD6959	Discontinued
0.6463	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD5647	Approved
0.6455	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD1549	Phase 2
0.6452	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6166	Phase 2
0.6442	Remote Similarity	NPD1876	Approved
0.6438	Remote Similarity	NPD17	Approved
0.6437	Remote Similarity	NPD3887	Approved
0.6436	Remote Similarity	NPD7054	Approved
0.6436	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD2438	Suspended
0.6433	Remote Similarity	NPD6099	Approved
0.6433	Remote Similarity	NPD6100	Approved
0.6433	Remote Similarity	NPD2935	Discontinued
0.6432	Remote Similarity	NPD7315	Approved
0.6429	Remote Similarity	NPD7058	Phase 2
0.6429	Remote Similarity	NPD7768	Phase 2
0.6429	Remote Similarity	NPD7057	Phase 3
0.6429	Remote Similarity	NPD4140	Approved
0.642	Remote Similarity	NPD3972	Approved
0.642	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD2313	Discontinued
0.6407	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7472	Approved
0.64	Remote Similarity	NPD4107	Approved
0.6395	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6385	Approved
0.6389	Remote Similarity	NPD6386	Approved
0.6386	Remote Similarity	NPD7435	Discontinued
0.6383	Remote Similarity	NPD7228	Approved
0.638	Remote Similarity	NPD5327	Phase 3
0.6379	Remote Similarity	NPD3750	Approved
0.6379	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5353	Approved
0.6364	Remote Similarity	NPD2403	Approved
0.6364	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD6653	Approved
0.6344	Remote Similarity	NPD7229	Phase 3
0.6343	Remote Similarity	NPD2309	Approved
0.6335	Remote Similarity	NPD7251	Discontinued
0.6319	Remote Similarity	NPD1465	Phase 2
0.6319	Remote Similarity	NPD1608	Approved
0.631	Remote Similarity	NPD5242	Approved
0.631	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD7808	Phase 3
0.6296	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD5735	Approved
0.6294	Remote Similarity	NPD1933	Approved
0.6294	Remote Similarity	NPD447	Suspended
0.6291	Remote Similarity	NPD7907	Approved
0.6287	Remote Similarity	NPD4482	Phase 3
0.6284	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6797	Phase 2
0.6283	Remote Similarity	NPD5953	Discontinued
0.6279	Remote Similarity	NPD1510	Phase 2
0.6278	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD8361	Approved
0.6276	Remote Similarity	NPD8360	Approved
0.6276	Remote Similarity	NPD8435	Approved
0.6274	Remote Similarity	NPD4111	Phase 1
0.6273	Remote Similarity	NPD5585	Approved
0.6272	Remote Similarity	NPD6663	Approved
0.6271	Remote Similarity	NPD1511	Approved
0.6264	Remote Similarity	NPD6280	Approved
0.6264	Remote Similarity	NPD6279	Approved
0.6263	Remote Similarity	NPD7286	Phase 2
0.6258	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD5710	Approved
0.6257	Remote Similarity	NPD1607	Approved
0.6257	Remote Similarity	NPD5711	Approved
0.6257	Remote Similarity	NPD6353	Approved
0.625	Remote Similarity	NPD7240	Approved
0.625	Remote Similarity	NPD6190	Approved
0.6238	Remote Similarity	NPD7930	Approved
0.6238	Remote Similarity	NPD6781	Approved
0.6238	Remote Similarity	NPD6779	Approved
0.6238	Remote Similarity	NPD6778	Approved
0.6238	Remote Similarity	NPD6780	Approved
0.6238	Remote Similarity	NPD6776	Approved
0.6238	Remote Similarity	NPD6782	Approved
0.6238	Remote Similarity	NPD6777	Approved
0.6235	Remote Similarity	NPD1240	Approved
0.6235	Remote Similarity	NPD4307	Phase 2
0.6235	Remote Similarity	NPD2979	Phase 3
0.6225	Remote Similarity	NPD7698	Approved
0.6225	Remote Similarity	NPD7696	Phase 3
0.6225	Remote Similarity	NPD7697	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data